Bromine → Methyl 2-amino-5-bromo-3-nitrobenzoate

HRID 12253Notes

Reaction equation

HRID 12253 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:13].[Br:15]Br>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([Br:15])[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 17984898Methyl 2-amino-5-bromo-3-nitrobenzoateYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2.23 g (10.4 mmol) of 2-amino-3-nitro-benzoic acid methyl ester in 12 mL of acetic acid was added dropwise over 5 minutes a solution of 0.53 mL (10.4 mmol, 1 eq) of bromine in 2 mL of acetic acid. The mixture was stirred at room temperature for 30 minutes and poured into 100 grams of ice. The precipitated yellow solid was collected by suction filtration and dried to afford 2.50 g (82%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ 3.95 (s, 3H), 8.35 (br s, 2H), 8.6 (d, 1H).

Workup

  1. filtrationThe precipitated yellow solid was collected by suction filtration
  2. customdried

Sources & evidence

ORD record
ord-becf597f931c48eab6d0ab9385f0ebff
Source dataset
uspto-grants-2010_06
Patent number
US07727992B2

Reaction notes

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